期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 4, 页码 2219-2233出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03203
关键词
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资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2016-76155-R, CTQ2017-85093-P]
- FEDER
- Generalitat Valenciana [PROME-TEOII/2014/017]
- University of Alicante
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
The addition of 2-bromobenzylmagnesium bromide to chiral N-tert-butanesulfinyl imines derived from tetralone-type ketones proceeds with high levels of diastereocontrol. The resulting sulfinamide derivatives were transformed into dibenzoazaspiro compounds after a palladium catalyzed intramolecular N-arylation. DFT calculations have been performed to rationalize the stereochemical course of the reaction. Similar results have been obtained considering either diethyl ether or toluene as a solvent, in both cases in an excellent agreement with experimental findings. NCI topological calculations have also been used to evidence crucial noncovalent interactions. In addition, the azaspiro compounds reduced the viability of chronic myeloid leukemia cells in the micromolar ;range. Notably, both the halogen-substituted (R)- and (S)-8g and -8h as well as (R)-8j were at least two times more effective on a multidrug-resistant derivative than on the parental cell line, exerting a collateral sensitivity effect.
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